Triethylamine → 4-(3-Phenyl-5-isoxazolyl)-1-butanol

HRID 1097719Notes

Reaction equation

HRID 1097719 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:11]([OH:17])[CH2:12][CH2:13][CH2:14][C:15]#[CH:16].C(N(CC)CC)C>C(Cl)Cl>[C:4]1([C:3]2[CH:16]=[C:15]([CH2:14][CH2:13][CH2:12][CH2:11][OH:17])[O:1][N:2]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 702345-Hexyn-1-olHCID 2756315N-hydroxybenzenecarboximidoyl chloride

Product 1

HCID 593956044-(3-Phenyl-5-isoxazolyl)-1-butanolYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To N-hydroxybenzenecarboximidoyl chloride (622 mg, 4 mmol) in dry DCM (6 ml) was added 5-hexyn-1-ol (431 mg, 4.4 mmol). The mixture was cooled to 0° C. under nitrogen as triethylamine (0.612 ml, 4.4 mmol) was added dropwise over 10 min. Stirred for a further 20 min at 0° C. then at room temperature overnight. The mixture was washed with water and the organic phase evaporated. The product was purified by silica SPE (20 g) eluting with EtOAc-cyclohexane (1:2, then 3:1) to give a white waxy solid (443 mg).

Workup

  1. additionwas added dropwise over 10 min
  2. customat room temperature
  3. customovernight
  4. washThe mixture was washed with water
  5. customthe organic phase evaporated
  6. customThe product was purified by silica SPE (20 g)
  7. washeluting with EtOAc-cyclohexane (1:2

Sources & evidence

ORD record
ord-5de4f5964fdb4079a5b7e04c6bd83c28
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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